Wake up to the sound of waves, step onto your private balcony with panoramic ocean views, and spend your days lounging by the pool, exploring scenic bike trails, or dining at waterfront restaurants.
Nothing says ultimate coastal getaway quite like Hilton Head Island. With pristine beaches, world-class golf courses, and endless outdoor adventures, this Lowcountry gem is the perfect destination for travelers craving sun, sand, and relaxation.
Whether you’re looking for a luxurious oceanfront estate, a private island retreat, or a stylish beach house with stunning beach views, we’ve rounded up the 6 best Hilton Head Airbnbs—each offering unbeatable beach views and direct access to the sand.
Buck Island
7 Bedrooms | 26 Guests
An entire private island. A boat ride to your front door. A once-in-a-lifetime escape. Experience all that in Buck Island, Hilton Head’s most exclusive rental property—where you don’t just stay by the water, you stay on it!
This 10-acre island retreat is a secluded paradise, complete with luxury accommodations, adventure-filled amenities, and total privacy for you and your crew. Getting here? Easy. Enjoy a quick 8-minute boat ride from Harbor Town Marina, with daily transportation included.
Want to go all out? Rent a private pontoon cruiser for the week or book a helicopter tour straight from the island’s private helipad!
Key Amenities:
✔ Exclusive 10-acre private island with complimentary boat transportation
✔ 10,000 sqft. main house + guest house (7 bedrooms, sleeps 26)
✔ Private pool & hot tub
✔ Crow’s nest lookout with 360° island views
✔ Koi pond & atrium built around a live oak tree
✔ Golf carts, outdoor games & a game room (pool table, foosball & more!)
✔ Helicopter tours are available directly from the island
✔ Daily boat rides to and from Hilton Head included
✔ Fridge stocked before arrival & 24/7 onsite caretakers (optional privacy available)
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South Beach Serenity
6 Bedrooms | 14 Guests
Who’s ready for the ultimate beachfront bash? Get ready to soak up some peaceful luxury! South Beach Serenity is your front-row seat to paradise in Hilton Head that offers direct beach access.
Wake up to panoramic ocean views and start your day lounging by the private pool or sipping coffee on the elevated sun terrace—the perfect spot to take in the sea breeze. The floor-to-ceiling windows create a bright, airy ambiance inside the house, with plenty of cozy seating areas for gathering.
Find the perfect balance of comfort and tranquility, an invitation to experience the laid-back vibes.
Key Amenities:
✔ Beachfront location with direct access
✔ Private pool & spacious patio for lounging
✔ Elevated sun terrace with ocean views
✔ Dedicated movie room with plush, sectional seating
✔ Chef’s kitchen with barstool seating & dining area
✔ Six elegant bedrooms (some with ensuite baths & outdoor access)
✔ Easy parking (up to 8 vehicles) & in-home laundry
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Sand Piper
4 Bedrooms | 8 Guests
They just don’t make them like this anymore. Sandpiper is a true Hilton Head gem—a historic beachfront retreat that meets coastal serenity. Tucked among towering trees for privacy yet just steps from the sand, this timeless beach house invites you to experience the simple pleasures of island life.
Inside, painted wood walls, soft interiors, and vintage details create a cozy yet airy atmosphere. Every corner inside the house tells a story, and outside, a picturesque backyard is made for slow, sun-soaked days. And when the stars come out, gather on the deck with a nightcap and let the ocean breeze lull you into relaxation.
Sandpiper is the perfect home base for coastal nostalgia and unforgettable beach days.
Key Amenities:
✔ Beachfront location with direct access
✔ Private balcony with rocking chairs
✔ Foosball table in a sunroom
✔ BBQ grill & outdoor dining area
✔ Hammock & shaded lounging spots
✔ Old-fashioned kitchen & cozy fireplace
✔ Spiral staircase & unique vintage decor
✔ Quiet, tree-shaded lot for extra privacy
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20 Bradley Circle
10 Bedrooms | 20 Guests
Luxury, space, and direct beach access—it doesn’t get better than 20 Bradley Circle. This newly built, multi-million dollar estate is set in Hilton Head’s exclusive Singleton Beach. Whether you’re planning a family reunion, corporate retreat, wedding, or group getaway, this home delivers one-of-a-kind comfort, convenience, and stunning ocean views.
Start your day by taking a dip in the infinity pool while the sea breeze drifts in. Inside, the open-concept living space features designer finishes with bedrooms enough for your entire group to spread out in absolute luxury.
For an unforgettable island escape, stay at 20 Bradley Circle and maybe have a chance of seeing dolphins!
Bonus: Need a bigger space for your large group? You can also rent out the Bradley Circle Buyout, which can cater to 48 guests with 20 bedrooms!
Key Amenities:
✔ Direct private beach access via boardwalk
✔ Infinity pool & poolside lounge
✔ Four covered balconies with coastal seating areas
✔ 10 spacious bedrooms, each with a private ensuite bathroom
✔ Two full kitchens & formal dining for 14
✔ Fourth-floor entertainment space with in-home bar & dining area
✔ Two laundry rooms & dedicated office for remote work
✔ In-home elevator (available Apr 2025) for added convenience
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Lido
6 Bedrooms | 16 Guests
At Lido, the only thing better than the beachfront location in Hilton Head is the endless ways to enjoy it. A stunning retreat perfect for large groups where you can wake up to ocean views and enjoy your morning coffee on the spacious balcony or step right outside and sink your toes into the sand.
But it’s the unexpected extras that make this home truly unforgettable—because where else can you find an indoor putting green, billiards table, and a private beachfront pool and hot tub all in one place?
Every moment at Lido is designed for laid-back luxury as your ultimate oceanfront getaway.
Key Amenities:
✔ Beachfront location with direct access
✔ Private pool & hot tub facing the ocean
✔ An indoor putting green
✔ Billiards table for friendly competition
✔ Full chef’s kitchen for group dining
✔ Multiple balconies with ocean views
✔ Modern coastal design & soft furnishings
Book on AvantStay Direct (Best Price!)
Beachwalk
6 Bedrooms | 16 Guests
Waking up to sunrise and ocean views, sprawling outdoor spaces, and a prime location just a block from Singleton Beach, Beachwalk is a coastal retreat designed for unforgettable group getaways. Overlooking the scenic wetlands, this three-story Lowcountry escape with beachy vibes and Southern charm offers the perfect setting for relaxation and adventure.
Spend your days taking in ocean breezes from the upper balconies or strolling down to the pier overlooking the nearby stream. Inside, the fun keeps going with an entertainment space filled with games.
Time to get your toes in the sand and your heart pumping for an amazing coastal trip.
Key Amenities:
✔ Stunning ocean & wetland views
✔ Private pool & hot tub for ultimate relaxation
✔ Spacious balconies with ocean-facing seating areas
✔ Game room with a pool table, foosball, & shuffleboard
✔ Outdoor pier
✔ Large chef’s kitchen & outdoor grill
✔ Bright, airy interiors with coastal-inspired decor
Book on AvantStay Direct (Best Price!)
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Seasonal Activities and Events in Hilton Head
Hilton Head Island offers a diverse range of activities and events throughout the year, catering to different interests and preferences. Here’s a breakdown of what you can expect during each season.
Summer (June to August)
Winter (December to February)
Spring (March to May)
Fall (September to November)
Key Takeaways
These top-tier vacation rentals combine luxury, comfort, and convenience, making your Hilton Head escape one to remember.
Beach Front:
With Beach Access:
Escape to Oceanfront Luxury
Wake up to sunrise ocean vistas, soak up the Southern charm, and enjoy endless opportunities for relaxation and adventure. Find your perfect Hilton Head retreat and book an unforgettable escape.
